How To Eat For Free in Chicago

I have always been known to be a penny-pinching cheapskate thrifty person since young. I bargain for prices when I shop at street markets in Thailand, Vietnam and Taiwan. 90% of my clothes and bags are bought during discounts, out of which about half of them are bought at over 50% off. In my opinion, there is nothing much to be that happy about when you look good in branded clothing given that you paid so much for it. And frankly speaking is it worth it? It is only an achievement when you manage to buy quality clothing that makes you look good, but at a fraction of the original prices.

Well, given that I am already so frugal or rather calculative even when I was earning a full-time pay, I guess it is quite expected that my penny-pinching abilities have gone one step higher when I no longer have a full-time salary in Chicago.

I only realise how much free food I have been getting in Chicago when a friend in Singapore commented on it after seeing numerous pictures of the free meals I gleefully shared with her. I think I have managed to get about 150 USD worth of free food over a span of 7 months in Chicago, and it is quite amazing even to me.

While I have always been able to source for good bargains everywhere I go, getting free food on a regular basis is a first to me. I think I surpassed myself, hahaha.

1.) Follow the Facebook pages of food establishments you like

As I think back to how I unwittingly managed to get free food, I think one important reason is that I check the Facebook pages of the food establishments I like regularly.

Because of this, I am always quite updated when it comes to their promotions and managed to score freebies every now and then. For example, there was once when I chanced upon a post on Chipotle’s Facebook page that said they are offering a promotion where you can redeem a free bowl from Shophouse (their sister restaurant) as long as you show a receipt from Chipotle. As I often buy rice bowls from Chipotle, I managed to dig out old receipts from Chipotle and in the end redeemed 2 free rice bowls from Shophouse worth about 18 USD in all.

As I am typing this, I got a new text message from Chipotle offering me a buy one free one promo code. Yippee!

For me, I receive free food vouchers from food establishments in my mailbox every now and then. This is quite surreal to me, because these food establishments simply give out free meal vouchers without asking for minimum spending which doesn’t ever happen in Singapore. I understand that they are doing promotion, even so they are really generous!

As these vouchers often have deadlines, therefore it is important to check your mailbox regularly so that you don’t miss out on a free meal.

Most importantly, you need to look at your mail properly. I believe a lot of people just throw away such free meal coupons without properly looking at it, thinking that it is just a typical advertisement pamphlet because there were times when I looked in the trashcan and spotted many free meal vouchers inside.

Which brings me back to the point of checking your mailbox regularly. If you check it daily, you will spot the free meal vouchers lying around the mailbox area, left behind by your neighbours. You can pick up the free meal vouchers before it is cleared away by the cleaner ! ( Please do not judge me)

3.) Take part in lucky draws held by food establishments

Every now and then, food establishments will hold lucky draws, sometimes it is for a free trip somewhere, and sometimes it is a pair of tickets for some concert. Naturally, you will feel that there is no way you can possibly win it. In fact, I feel the same way too.

However, the point of joining such lucky draws is not to win the free trip, but to win free meals. Sometimes, the food establishment will send you a text message or email to offer you a free meal when you did not win the free trip.

I entered a lucky draw before and in the end I received a code to redeem a free meal, even though such a freebie wasn’t stated when I joined the lucky draw. And the interesting thing is, I didn’t receive spam or promotional messages from the food establishment after I joined the lucky draw, I only receive a message when I get to redeem a free meal. So there is really no harm in taking part in such lucky draws.

4.) Read fine prints carefully when you take part in events

Many times, the organising team of a public event will have partnerships with food and drink establishments. Therefore such partners might have promotions for attendees of that event, and the details might be in the fine print of the event brochure.

I will just take an event I attended recently as an example. I was looking for interesting stuff to do on a Friday and I spotted this Activate event organised by the Chicago Loop Alliance. I checked out the website of this event to get a sense of what is it about, but in the end it was the freebies that enticed me to attend. LOL.

Apparently, in a bid to get visitors to explore the loop area, the alliance had several partnership deals with neighbouring restaurants and theatres. And the one that caught my attention was the partnership with Nandos whereby you can redeem a free quarter chicken when you show your event wristband.